Tandem Photoredox-Chiral Phosphoric Acid Catalyzed Radical–Radical Cross-Coupling for Enantioselective Synthesis of 3-Hydroxyoxindoles
Yang Zhang, Dan Ye, Lei Shen, Kangjiang Liang, Chengfeng Xia
Abstract
A photochemical protocol that couples diarylamines and α-ketoesters to afford the chiral 3-hydroxyoxindoles through tandem photoredox and chiral phosphoric acid catalysis is developed. The reaction involves an enantioselective photochemical radical-radical cross-coupling process. The chiral phosphoric acid is discovered to play crucial roles by decreasing the reductive potentials of α-ketoesters and stereocontrolling the downstream asymmetric radical-radical cross-coupling via the formation of pentacoordinate complex.
Topics & Concepts
ChemistryPhosphoric acidEnantioselective synthesisTandemPhotoredox catalysisCatalysisPhotochemistryCombinatorial chemistryOrganic chemistryPhotocatalysisMaterials scienceComposite materialRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry